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The essay explores President Trump’s emerging immigration enforcement strategies in context. It starts with a look back at the “lonely” years of immigrant activism. Part I of the Essay explains the enforcement landscape the Obama Administration inherited and the evolution of that Administration’s own enforcement policies. This Part surveys the lessons learned — and not learned — by the Obama Administration. Part II of the Essay details the new Administration’s enforcement efforts, including the thwarted January 27, 2017 executive order containing the now infamous travel ban on certain foreign nationals and refugees, his March 6, 2017 executive order replacing the January ban, and the interior immigration enforcement efforts mapped out in two January 25, 2017 orders along with their implementing Department of Homeland Security memoranda of February 20, 2017. This analysis reveals the extent to which President Trump’s policies constitute a doubling-down on some of the least productive and most discredited approaches to enforcement.